Commercial Transportation Underwriter

Our client is a growing and well-established Managing General Agent (MGA) specializing in commercial insurance solutions across Canada. Due to continued growth within their transportation portfolio, they are seeking a Commercial Lines Underwriter to join their underwriting team.

This opportunity is ideal for an underwriting professional who enjoys working with complex commercial transportation risks, building strong broker relationships, and contributing to a collaborative, growth-oriented environment. The successful candidate will receive direct mentorship from experienced industry leaders while gaining exposure to specialized transportation and captive insurance programs.

Key Responsibilities

• Underwrite and manage a portfolio of medium to large commercial transportation and fleet accounts
• Evaluate and quote new business, renewals, endorsements, and policy changes
• Analyze risk exposures and make underwriting decisions within delegated authority levels
• Negotiate terms, conditions, and pricing with broker partners
• Build and maintain strong relationships with brokers and key stakeholders
• Support profitable portfolio growth through sound underwriting practices
• Provide technical guidance and mentorship to junior underwriting staff
• Assist with the ongoing development and enhancement of underwriting guidelines, processes, and workflows
• Collaborate with claims, operations, and leadership teams to ensure exceptional service delivery
• Represent the organization at broker meetings, industry events, and networking functions as required

Qualifications

• Minimum 3 years of Commercial Auto or Commercial Transportation Underwriting experience
• Experience underwriting medium to large transportation fleets preferred
• Strong analytical and decision-making abilities
• Excellent communication and relationship-building skills
• Ability to thrive in a collaborative, fast-paced underwriting environment
• CIP designation completed or in progress is preferred
• RIBO license or willingness to obtain one is considered an asset
• Exposure to domestic markets and Lloyd’s placements is considered an asset

What’s Offered

• $75,000 - $105,000 base salary + performance-based bonus
• Comprehensive health and wellness benefits package
• Retirement savings program
• Generous paid time off
• Tuition reimbursement and support for professional designations
• Ongoing mentorship from experienced underwriting leaders
• Collaborative team culture with strong internal support
• Long-term career growth opportunities within a growing MGA platform

Ideal Candidate
This role is well-suited for an underwriter who:

• Enjoys transportation and commercial fleet underwriting
• Wants to deepen their technical underwriting expertise
• Values mentorship and professional development
• Thrives in a collaborative, team-oriented environment
• Is looking for long-term career growth within the MGA space

At Aplin - together with our brands CompuStaff, Impact Recruitment, and Vantix Systems - we connect great people with great organizations across North America. We believe diverse teams build stronger companies, and we welcome applicants from all backgrounds, experiences, and perspectives. We use AI tools to assist in a fair and efficient matching process, helping our recruiters connect the right people with the right opportunities. To be considered, applicants must be legally entitled to work in Canada, including holding any required permits. Our recruitment services are always free for job seekers.